(4-Benzenesulphonyl-6-bromopyridin-2-yl)-methylamine → (4-Benzenesulphonylpyridin-2-yl)-methylamine

HRID 1603550Notes

Reaction equation

HRID 1603550 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[C:14](Br)[N:13]=[C:12]([NH:17][CH3:18])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:17][CH3:18])[CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 15410397(4-Benzenesulphonyl-6-bromopyridin-2-yl)-methylamine

Product 1

HCID 15410398(4-Benzenesulphonylpyridin-2-yl)-methylamineYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.09 g (0.000275 mol) of (4-benzenesulphonyl-6-bromopyridin-2-yl)-methylamine was dissolved in 7 ml of ethanol, treated with 0.009 g of Pd/C (10%) and hydrogenated under normal pressure for 18 hrs. Thereafter, the catalyst was filtered off, the solvent was removed and the residue was partitioned in ethyl acetate and saturated bicarbonate solution. The organic phase was washed with sat. sodium chloride solution and dried over MgSO4. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:4 and 1:3. There was obtained 0.025 g (37%) of (4-benzenesulphonylpyridin-2-yl)-methylamine as beige crystals; m.p.: 142-143° C.

Workup

  1. filtrationThereafter, the catalyst was filtered off
  2. customthe solvent was removed
  3. customthe residue was partitioned in ethyl acetate
  4. washThe organic phase was washed with sat. sodium chloride solution
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent the residue
  7. customwas chromatographed on silica gel with ethyl acetate/hexane 1:4 and 1:3

Sources & evidence

ORD record
ord-512af824325540de941a68cc448b03dc
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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